I recently interviewed TaskRabbit CEO Ania Smith on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam Mendler: Our guest today is the leader of one of the leading online marketplaces for freelancers. Anya Smith is the CEO of TaskRabbit, where hundreds of thousands of freelancers have performed millions of tasks in thousands of cities across nine countries. Anya, thank you for joining us.

Ania Smith: Thank you so much for having me. Excited to be here.

Adam Mendler: Excited to have you on. You grew up in a small town in Poland and you moved to Sioux Falls, South Dakota with your parents when you were twelve. You didn't speak any English at the time. Your parents didn't come to the US. With a whole lot. You started working when you were in junior high into high school. To chip in. Can you take listeners back to your early days? What early experiences and lessons most significantly shaped your worldview and shaped the trajectory of your success?

Ania Smith: So it's one of these stories where it can seem harsh at the time, but honestly, looking back, it's definitely shaped who I am and has shaped some of my key values and key principles and how I think about just life in general. And so when we moved to the US. It wasn't so much that I needed to help with the bills, but I really needed to pay for my clothing and I needed to pay for things that I wanted to have. And so that meant I needed to figure out how to make money quite quickly. And so I started the way many people started in their first job, which is to have a paper route. And I didn't need to speak much English and I could understand what the addresses meant, and it meant getting up really early in the morning in a freezing cold in South Dakota. But I loved getting paid and then knowing that I have control and I can decide what to do with that money. And it was really powerful. And so fairly quickly I started thinking about how I could make more money than just off the paper route. And the laws are what they are for a reason. So at 14, I had to wait till I was 14. I started with another job, which was working at a fast food joint. And all of these things just taught me so many valuable lessons. One of which is grit. Another one is hard work. Another one is just learning quite quickly how to show up on time and how to do my best work and how important it is to form relationships and how important it is to get to know your customer and really be able to serve the customer and understand their needs. Sometimes the customers are not so nice and so these are important lessons that end up coming forward for life, really. I have been in consumer based industries for a very long time. I feel that it's really helpful for me to lean back on those experiences from early days when I first moved to the US.

Adam Mendler: Grit, hard work. Being there, showing up, being present, giving your best every single day. The power of relationships. The importance of customers. Customer centricity essential to building any successful business. How can leaders build truly customer centric businesses?

Ania Smith: I think there is really no other way to do it than to spend time with your customers as much as possible. So obviously, when I'm working at the front cash register, I'm based with customers day in and day out. My next job was moving up when I turned 16, into waiting tables, because that definitely was more lucrative. But the customers also became more demanding. And you learn a lot about what's important to people. You learn a lot about how customers are very different and what some like, others dislike. And you learn a lot about understanding how to negotiate and how to make sure that they have a really good experience. And so that has carried me through for years.

Ania Smith: And so before I got to TaskRabbit, my two previous opportunities were at Airbnb and at Uber. And it was very important for me, as it is today, to really understand and learn the product and spend as much time as possible with our customers. And so at Airbnb, I was very much so focused on the hosts. And so I would spend a ton of time with our hosts, meeting them all over the US. But really also in Europe and elsewhere in Australia, and learning about what's important to them and what they really care about. And I tell you, even after you meet hundreds and you have what seems like infinite number of conversations, it's always amazing that almost every time you learn something new. I also became a host because I felt it was really important to understand how that would work. What is it like to have people come and spend the night in your own house? And so when I moved on to Uber, I also spent a lot of times really caring and working with our couriers.

Ania Smith: I was heading the supply operations for couriers at Uber Eats. And so not only would I spend a lot of time just understanding what is motivating to our drivers, but I spent a lot of time delivering food myself. Because that, again, is one of the only ways that you can really truly understand the needs of the customers. And the same thing goes for TaskRabbit. It's really important for me to spend time with our taskers and to spend time as a client, booking tasks fairly often and meeting more taskers, and understanding what they love about our platform and what are some things that we can get better at. That's the best way to learn about how to grow your business.

Adam Mendler: Know your customer intimately, get personally invested, go to the ground level, be there back to being present. Another great tip be a customer. Understand your product from that perspective. If you run a restaurant, order your own food and be honest about what the food tastes like. How is the service, how's the atmosphere, how's the environment? In your case, you were an Airbnb host. You have been a customer of TaskRabbit in addition to being the CEO of TaskRabbit. That's something that can be applied to everyone, regardless of whatever business they're in.

Ania Smith: I couldn't agree more. And oftentimes it's said we spend a lot of time making PowerPoint presentation, google Slides and Decks and Strategizing, and these things are important. But spending time on the ground with your customers are really critical.

Adam Mendler: What were the keys to rising within your career? And what can anyone do to rise within their career?

Ania Smith: It's several things, really. It's about understanding what you'd like to do, what you want to do, and I think that's really hard. People often say, follow your passion, but many of us don't really know what our passion is, or it can't be so clearly or quickly defined. But it is important to understand what you think you want to do and try to get to that answer at some point. But separately, it's important to understand what you're good at. And I may want to be an artist and I may want to be a singer, but if I started singing, most people would want to run out of the room. So even though I may want to do it, I'm certainly not good at it. And so understanding what I may be good at is another overlay plus what you think you want to do.

Ania Smith: Another piece that I think about is what do you think that the world needs? How can you be passionate about using your skills to make the world better in some sense? And then finally, the fourth component. This may not be important for everyone. For me, having grown up with fairly limited needs, understanding what I can get paid for and what would actually make money was very important. I wanted to make sure that I, as an adult, lived in a different way, and I also wanted to make sure to provide a different environment for my children. And so these four components have driven my thinking about what I want to do or really how to succeed in my career. There are other pieces that we've already talked about, which is hard work and curiosity and so many other components. But this is how I've been driven in trying to decide how I can best add to the world.

Adam Mendler: I'd love to dive into some of those elements. What advice do you have for listeners on how to understand what it is that you're truly great at? How to understand what it is that you're truly passionate about? You might be passionate about football, but does that mean that you're going to be the starting quarterback for a football team? Or does that mean that you should work in football? Or does that mean that you have some passion that might be somewhat connected to football, that you could apply to a different industry? How do you figure out what the world needs and how you can get paid for it? What would you share?

Ania Smith: All of those examples are perfect examples in really trying to think, okay, well, where do I start? And some of these clues we get fairly early on, even in high school. And below you can start understanding that I really enjoy doing geometry, but reading classics is not really something that I'm liking right now. That doesn't mean that you are not going to go into journalism, perhaps try a different professor in college or a different discipline to see if that's something you enjoy early on. It's really important to test a lot of things, and I sometimes get disappointed or discouraged when I see people so very early on just focusing on one thing, because it's really hard, generally speaking, when we're young, we don't know what we want to do. And so having this freedom to go in few different directions and quickly change course if it's not something exciting or if you don't find that you're passionate about it, or if everyone around you tells you, hey, I get it. You really want to be a football player. But I got to tell you, you just don't have the skills that are needed. And relative to everyone else, it's hard to see whether you may have skills that are needed.

Ania Smith: But you know what? Actually we're looking for some folks who are really good at analyzing plays or are really good at thinking about sponsorships for football players. And maybe that's something that you can do. And so early on in your career and really in college, it's really great to have some ability to go and try a few things in different directions and see what gets you excited and listen to others who say, wow, you're really amazing at this. Or did you realize that when you do that, you do a really great job? Those are sometimes external hints that can be very helpful.

Adam Mendler: I love it, and I think it's very applicable to people in the early innings of their career, but I think it's also applicable to people who are in the middle of their career, people who might be later on in their career thinking about what's next. For me, maybe there's another career I could transition into. And it's never too early or too late to get on this journey, this journey of self discovery, this journey of understanding. What is it that I'm great at? What is it that I love? What is it that energizes me, that fuels me, that gets me going, that drives me? And it's amazing if you could figure that out when you're a college student, but if you haven't figured it out when you're a college student. Doesn't matter. Figure it out when you're 25, 35, 45, 55. Just get going. Just get started. Just do it.

Ania Smith: I couldn't agree more. And about halfway through my career, I decided that I wasn't quite sure whether what I was doing was giving me the energy that I thought I needed. And so actually I decided to take a career break for a year and quit my job. And I understand it's very privileged, but we had been saving for something like that as a family for quite some time. And we took a year off and we moved to a different continent. We moved to Argentina with our family and really spent a lot of time during that year trying to be very intentional about the decisions that we're going to make about the next phase of our careers. And so for myself, I really explored multiple different avenues. I thought, well, do I want to stay in tech? There's some amazing things about being in technology and being in the Bay Area and being surrounded by all the startups and all that that brings.

Ania Smith: But I spent a lot of time thinking about whether or not this is something that I wanted to keep doing. I explored other opportunities. I thought about moving to much smaller towns. We thought about having very different roles and different jobs in different industries, perhaps some that were maybe less lucrative, but offered something else. We thought about moving to different countries and so on. And it was very liberating to intentionally make a decision to in fact come back to the Bay Area where we feel it's our home and where we definitely love the people and the culture and the weather and everything else, and be very intentional about how we design the next phase of our career. And so for me that meant going back to tech and also meant staying in marketplaces. Because I had found that working in a marketplace was extremely challenging, super analytical.

Ania Smith: It was new space. I loved the people who were also interested in solving these types of problems. And so it was fabulous to have the freedom to do that. And I would say that this happened in 2019. And so when a pandemic hit, I was at Uber, and it was great to see many people go through that evaluation themselves. And I felt that the pandemic was sort of a motivator to do that. I felt already quite settled because I had gone through that exercise for the previous twelve months where I was very content in the decisions that we had made as a family and I had made in terms of my career about what I wanted to do next. I really would encourage people to not just let the status quo direct your life, but instead be much more deliberate about the choices that you make.

Adam Mendler: Take ownership. It's your life. You only have one life and it's yours. Get in the driver's seat. You just shared a really big decision that you wrestled with as a CEO, you're constantly making important decisions. Can you describe your framework around making difficult decisions and your best advice on the topic of decision-making?

Ania Smith: Yeah, so I think actually that's changed a lot over time. I would say when I was younger, both in my professional life but also in my personal life, I would leverage data a lot and think, well, if companies make decisions using data, I should also use data in my personal life and let that drive a lot of the thinking. Over time, I've realized that data is just one input and without sounding cliche, there is this intuition or gut feeling or ability to make sure that I'm hearing from different constituents and stakeholders and taking all of that information into account. And a spreadsheet will only tell me a little bit. There's so much more context and background and biases and previous decisions that go into the next decision that I try to learn and be as curious as I possibly can and ask a lot of questions. And then it's really important to be decisive and make that decision. After a while, there is no new information and I sometimes find people ask for new information as almost a tactic to delay that decision. But actually I truly believe that a bad decision is better than no decision because at least you will learn.

Ania Smith: And most decisions are very reversible, meaning you make a decision, you go in that direction and then fairly quickly, hopefully, you get to see if it doesn't work and you get to change course, which is why that's better than just making no decision. And so that's how I approach thinking about decisions.

Adam Mendler: And that's really good advice. I really love the way you framed it. That balance between curiosity and decisiveness driving you to making effective decisions and just making decisions. To your point, even if the decision proves not to be the right decision, you have to make one. And then having the open-mindedness to then reverse course if things don't go well brings up a lot of themes applicable beyond decision-making. Universal to effective leadership. Curiosity a key characteristic of the most effective leaders. Flexibility one of the most important characteristics among the most successful leaders in your experience, what are the most important characteristics among the very best leaders and what can anyone do to become a better leader?

Ania Smith: One of the most important characteristics we've already talked about, which is curiosity. It's really important to ask questions and be wanting to learn. Secondly, and just as importantly, is therefore being able to listen and take in that information, even when sometimes it's not great information. It's also really important to be able to change your mind. Sometimes people get stuck and to me it's critical to come back to the very basics and break down the problem and try not to get bogged down. And that's how it used to be or that's how we always did it, or that's how we do it, or that's how it worked last time. But break down into more of first principles thinking where you're really looking at the problem in a fresh way and you're open to having your mind change, that's very important. And then finally leading with empathy, which comes back to listening, but really being able to have the courage to step into someone else's shoes and understand the problem from their perspective.

Ania Smith: And that's not always easy to do. You have to have a lot of self-awareness and understand what are your weak spots and what are your strengths. And speaking of weak spots, you have to really be open to getting feedback from your team. And that's not always the most fun thing, especially sometimes the feedback is not always as positive as you'd hope. It's really the only way to learn. So being okay with learning and failing and trying things again and having that resilience is super important. These are really not just lessons for leadership, but these are lessons I try to instill in my kids as well. Resilience is one of the most important characteristics that one can have as a human.

Adam Mendler: It's a great list. Great leaders are great listeners. Great leaders lead with empathy, self-awareness, essential to effective leadership. The power of feedback can't be understated. Resilience. A key theme in so many of these episodes, so many conversations with so many of the most successful leaders have centered around the fact that there is no linear path to success. You're going to get knocked down. How do you view failure? How do you view setbacks? Are they terminal or are they bumps in the road? Are they learning experiences? Are they opportunities for you to get better? Was there a particular failure setback bump in the road? In the course of your life, in the course of your career? That has been a game changer for you in terms of the way that you lead.

Ania Smith: The list is very long. I can talk about maybe something small, but ends up being super important. When I first became a manager, it was really hard to understand the difference between what does it mean to be a manager, what does it mean to be a leader? And we are working on a project and it was an important project and I was leading a team of multiple people and we were asked to do something and I was asked to do this by my manager and I wasn't quite sure why we were doing it. I wasn't quite aligned with it. So then I met with my team and said, hey, we need to do this thing. And they asked why and I kind of sort of made something up or what I thought was the right why. And then I said something, well, we have to do this because my manager expects us to do this, which essentially meant I leverage his name in order to try to motivate and inspire people to do something that clearly I myself didn't yet know or understand or believe in. It is just a lazy way to lead people and it is not the right way.

Ania Smith: If you kind of want to lose their buy-in, the quickest way to do that is by saying because so and so told us to do it. And so I did that once, it then came back and my manager pulled me aside and gave me a quick lesson and I've never done that since. But I sometimes see or hear leaders do it and I've seen it throughout any organization. Until you understand that it actually works counter to what your objective is and you're not actually motivating or inspiring people because you yourself have to be able to explain the why. It is really important to motivate people by believing in something. Otherwise if you yourself don't believe in it, it's almost next to impossible to get others to follow you. And so coming back to understand the why and really being thoughtful and taking the time to explain it is really important.

Adam Mendler: I love that story for a variety of reasons. Firstly, the underlying lesson that you shared around motivation and the importance of everyone needing to understand why we do what we do as opposed to being told you need to do this because someone in a position of authority is telling you to do it. That's a great lesson. That's a powerful lesson. That's an important lesson. I also love the story because clearly that wasn't a game-changing moment in your life much in the way that spending a year in a foreign country would be. Much in the way that moving to the US at age twelve, not speaking the language that to me from the outside looking in would seem to be a game-changing moment, game-changing experience. But as a leader, being able to find opportunities to learn in all of these experiences, big and small, that lesson that you were able to pull from that moment invaluable, and just the fact that you're going and finding those lessons goes back to just how important self-awareness is to effective leadership.

Ania Smith: I agree. It's an ongoing journey, so I still have a lot to learn, and I still get tripped up a lot, and I still get feedback that says, hey, you didn't listen as well as you could have in this situation. And this is the way that impacted the team. And it's really important to create that kind of environment where people are open to feedback and are open to continue to learn and to change their mind.

Adam Mendler: What should leaders understand about gig workers and the gig economy?

Ania Smith: So I think that the world is definitely changing and the Pandemic has shown us this. So more and more people are becoming independent contractors because more and more of them are really wanting more flexibility in their lives. And we've seen these numbers growing over time and it's likely to continue to grow over time. And so that means people really want to find different ways of earning a meaningful income and being inspired and doing things that they're passionate about that don't require the very much more standard, either hourly work or a nine-to-five office job. And we're excited that TaskRabbit. We are able to provide opportunities for hundreds and thousands of independent contractors and small businesses of people who want to maybe take a break. Or maybe this is something that they want to do permanently. Or maybe they just need some extra cash on weekends.

Ania Smith: Or perhaps they just graduated from college and are unsure about their first permanent job. And this has given them a way to make a very healthy income. And so there are many use cases where many people are really excited about the type of opportunities that TaskRabbit provides. And I think this is only going to continue to grow.

Adam Mendler: Diversity and inclusion - deeply embedded into the core fabric of TaskRabbit - female-founded company, all of the CEOs in TaskRabbit history have been women, women hold 40% of leadership roles, 17% of employees identify as LGBTQ. 40% are black, indigenous and people of color. How can leaders build truly diverse and truly inclusive cultures? And in your experience, how does having such a diverse and inclusive culture impact your organization?

Ania Smith: So a couple of questions there. Let me start with the second one. We have to reflect who our customers are and the only way to do that is to build a diverse culture because our customers are very diverse. And so if we are sort of just one and look and act like one types of people, that's going to be a problem because we are not going to be able to understand what our customers want and need back to how we started the conversation. So it's very important to us that we reflect our customer base and that we continue to really focus on ensuring that we're having people from multiple backgrounds come and join us at TaskRabbit. How do we do that? I think it is about putting emphasis on it. So we have a very robust diversity and inclusion and belonging strategy where we have very clear goals, where we have very clear objectives and we measure ourselves against those objectives. And so that means, for example, when we're hiring, we want to make sure that we have a diverse pool, which sometimes it means that it takes longer to hire someone, but we know that we've gone through and really challenge ourselves to make sure that the pool of candidates comes from different backgrounds.

Ania Smith: And so there are multiple examples like this where you have to make the trade-offs. If this is important, there are ways to do this and to build in that way. Certainly having Stacey and Leah as my predecessors has helped. They were the ones who absolutely set the culture of diversity and its importance at the core of TaskRabbit, what it was then and what it is today and what it's going to continue to be. So I am very fortunate to follow them and to continue in that direction.

Adam Mendler: Anya, what can anyone listening to this conversation do to become more successful personally and professionally?

Ania Smith: Being a good listener and being curious and always be willing to learn and find new, different things to learn. Like right now, I'm learning how to play tennis. I've never played tennis, so it's really rough at my age to start. But I enjoy that 1 hour a week when I get to go on a court. And I am just focused on that. It's one of the few times where I'm not thinking about work, and I love that. I'm focused on trying to get my forehand to do what I wanted to do and really just thinking about something else. I have been forever trying to learn Spanish since my time in Argentina, and I'm still quite bad at it. But there are different of trying to challenge yourself always to be learning not just in your core, but doing things differently.

Adam Mendler: Ania, thank you for all the great advice and thank you for being a part of Thirty Minutes Mentors.

Ania Smith: Thank you so much. I really enjoyed it.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally-recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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